Synthesis of macrocyclic dithiadiperoxyspiroalkanes with the participation of lanthanide catalysts

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Abstract

An effective method has been developed for the synthesis of macrocyclic dithiadiperoxyspiroalkanes by cyclocondensation of alkane-α,ω-dithiols (butane-1,4-, pentane-1,5-, hexane-1,6-dithiols) with 1,1-dihydro-peroxycycloalkanes and formaldehyde with lanthanide catalysts.

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About the authors

N. N. Makhmudiyarova

Institute of Petrochemistry and Catalysis, Russian Academy of Sciences

Author for correspondence.
Email: natali-mnn@mail.ru
ORCID iD: 0000-0003-1952-4173
Russian Federation, prosp. Oktyabrya, 141, Ufa, 450075

I. R. Ishmukhametova

Institute of Petrochemistry and Catalysis, Russian Academy of Sciences

Email: natali-mnn@mail.ru
ORCID iD: 0000-0001-7964-5175
Russian Federation, prosp. Oktyabrya, 141, Ufa, 450075

U. M. Dzhemilev

Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Email: natali-mnn@mail.ru
Russian Federation, Leninsky prosp. 47, Moscow, 119991

References

  1. Dembitsky V.M., Ermolenko E., Savidov N., Gloriozova T.A., Poroikov V.V. Molecules. 2021, 26, 686. doi: 10.3390/molecules26030686
  2. Bu M., Yang B.B., Hu L. Curr. Med. Chem. 2016, 23, 383–405. doi: 10.2174/0929867323666151127200949
  3. Gollnick K., Griesbeck A. Tetrahedron Lett., 1984, 25, 4921–4924. doi: 10.1016/S0040-4039(01)91259-6
  4. Skold C.N., Schlessinger R.H. Tetrahedron Lett., 1970, 10, 791–794. doi: 10.1016/S0040-4039(01)97831-1
  5. Hoffman Jr.J.M., Schlessinger R.M. Tetrahedron Lett., 1970, 10, 797–800. doi: 10.1016/S0040-4039(01)97833-5
  6. Adam W., Wang X. J. Org. Chem. 1991, 56, 15, 4737–4741. doi: 10.1021/jo00015a030
  7. Jefford C.W., Currie J., Richardson G.D., Rossier J.-C. Helv. Chim. Acta, 1991, 74 (6), 1239–1246. doi: 10.1002/hlca.19910740612
  8. Makhmudiyarova N.N., Shangaraev K.R., Dzhemileva L.U., Tuymkina T.V., Mescheryakova E.S., D'yakonov V.A., Ibragimov A.G., Dzhemilev U.M. RSC Adv., 2019, 9, 29949–29958. doi: 10.1039/C9RA06372B
  9. Makhmudiyarova N.N., Ishmukhametova I.R., Shangaraev K.R., Dzhemileva L.U., D'yakonov V.A., Ibragimov A.G., Dzhemilev U.M. New J. Chem., 2021, 45, 2069–2077. doi: 10.1039/D0NJ05511E
  10. Махмудиярова Н.Н., Ишмухаметова И.Р., Ибрагимов А.Г., Джемилев У.М. Докл. акад. наук. 2020, 492–493 (4), 35–41. [Makhmudiyarova N.N., Ishmukhametova I.R., Ibragimov A.G., Dzhemilev U.M. Doklady Akademii Nauk. 2020, 492–493 (4), 35–41.] doi: 10.31857/S2686953520040044
  11. Tyumkina T.V., Makhmudiyarova N.N., Kiyamutdinova G.M., Meshcheryakova E.S., Bikmukhametov K.Sh., Abdullin M.F., Khalilov L.M., Ibragimov A.G., Dzhemilev U.M. Tetrahedron, 2018, 74, 1749–1758. doi: 10.1016/j.tet.2018.01.045
  12. Oda S., Franke J., Krishce M. J. Chem. Sci., 2016, 7, 136–141. doi: 10.1039/C5SC03854E
  13. Wellmar U. J. Heterocycl. Chem., 1998, 35, 1531–1532. doi: 10.1002/jhet.5570350653
  14. Krohn K., Cludius-Brandt S. Synthesis, 2010, 8, 1344–1348. doi: 10.1055/s-0029-1218658
  15. Vojacek S., Beese K., Alhalabi Z., Swyter S., Bodtke A., Carola Schulzke C., Jung M., Sippl W., Link A. Arch. Pharm., 2017, 350, e1700097. doi: 10.1002/ardp.201700097
  16. Terent'ev A.O., Platonov M.M., Ogibin Y.N., Nikishin G.I. Synthetic Commun., 2007, 37, 1281–1287. doi: 10.1080/00397910701226384

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